Cerniglia C E, Dodge R H, Gibson D T
Chem Biol Interact. 1982 Jan;38(2):161-73. doi: 10.1016/0009-2797(82)90037-0.
The filamentous fungus, Cunninghamella elegans, was found to metabolize the potent carcinogen, 3-methylcholanthrene (3-MC) to 1-hydroxy-3-MC, 2-hydroxy-3-MC, 1-keto-3-MC, 2-keto-3-MC and trans-9,10-dihydrodiols of 1-hydroxy-3-MC. In addition several unidentified derivatives of 3-MC were found. The metabolites formed were separated by high pressure liquid chromatography (HPLC) and identified by comparison of retention times, absorbance, fluorescence and mass spectra with those of synthetic standards. Incubation of (+/-)-1-hydroxy-3-MC and (+/-)-2-hydroxy-3-MC with cells of C. elegans indicated that 1-hydroxy-3-MC is metabolized to form diasteromerically related trans-9,10-dihydrodiols of 1-hydroxy-3-MC. Experiments with 3-[14C]MC showed that over a 48-h period, 8.7% of the hydrocarbon was oxidized to organic solvent-soluble metabolic products. Most of the metabolites were polar products, some of which co-chromatographed with trans-9,10-dihydrodiols of 1-hydroxy-3-MC. The results show that C. elegans has the ability to oxidize 3-MC to metabolites that have been implicated as proximate carcinogenic forms of 3-MC in higher organisms.
丝状真菌秀丽隐杆线虫被发现可将强效致癌物3-甲基胆蒽（3-MC）代谢为1-羟基-3-MC、2-羟基-3-MC、1-酮基-3-MC、2-酮基-3-MC以及1-羟基-3-MC的反式-9,10-二氢二醇。此外，还发现了几种未鉴定的3-MC衍生物。通过高压液相色谱（HPLC）分离形成的代谢产物，并通过将保留时间、吸光度、荧光和质谱与合成标准品进行比较来鉴定。用（±）-1-羟基-3-MC和（±）-2-羟基-3-MC与秀丽隐杆线虫细胞一起孵育表明，1-羟基-3-MC被代谢形成1-羟基-3-MC的非对映体相关反式-9,10-二氢二醇。用3-[¹⁴C]MC进行的实验表明，在48小时内，8.7%的烃被氧化为有机溶剂可溶的代谢产物。大多数代谢产物是极性产物，其中一些与1-羟基-3-MC的反式-9,10-二氢二醇共色谱。结果表明，秀丽隐杆线虫有能力将3-MC氧化为在高等生物中被认为是3-MC的近致癌物形式的代谢产物。
